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Organometallic compounds
Journal of Organometallic Chsnistry Elsevier Sequoia S.A., Lalisanne -Printed
ORGANOMETALLIC
COMPOUNDS
XXXVII”. MASS SPECTRA METHYLTIN HALIDES
M. GIELEN
281
in The Netherlands
OF MIXED
TETRAALKYLTINS
AND
OF TRI-
and G. MAYENCE
VniversitP Libre de Bruxelles, Faculre des Sciences, Collectifde Roosevelt 50,B1050 Braxelles (Belgium)
Chimie Organique Physique, Avenue F. D.
(Received June 7th. 1972)
SUMMARY
The mass spectra obtained for a series of compounds of alkyldimethyl-secbutyltin, alkyldimetbyl(a-methylbenzyl)tin, alkyltriisobutyltin and trimethyltin halides confirm the fragmentation rules described earlier.
Diastereotopic nonequivalence has been described for molecules of the type R’Me,SnCHY(CH,) with Y =C2H5, C6H5 and with various R’ groups’. The purpose of this paper is to describe the mass spectra of these compounds, and to compare the obtained results with the conclusions of previous studies3. Table 1 gives the observed fragmentions for a series of alkyl- and phenyldimethyl-set-butyltins. Table 2 presents the mass spectra of various dibutyldimethyltins. The results may be summarized in the following possible fragmentation pattern :
SnH’
_
SnH3* _
SnH+
(continued on p. 284) l
For part XXXVI see ref. 1.
J. Organometal. Chem., 46 (1972)
tn $ : 8 w s
R=Er
3.4 5.1 0.4 11.7 3.7 1.2 32.2(a) 2.5 21.3(b)
6.7(c) 1.5
32.2(a) 7.1 21.3(b) 6.7(c)
1.7
0.9
Frofpnenr
Sn+ SnH+ SnH.: MeSn+ MeSnH: Me$n+ Me,SnM + BuSn’ BuSnH: MeBuSnH+ Mc,BuSn’ RSn+
RSnH: MeRSnH’ Me,RSn + BuRSnH’
MeBuRSn +
Me,BuRSn + 0.3
1*1(c)
0.3 2,5(a) 14.0(b)
4.6 7.1 0.2 19.8 4.9 0.4 40.2 0.7 2.5(a) 14.0(b) 2.7 1,2
Pr
0.5
I .2(c)
0.3 2.5(a) 18,5(b)
3.4 7.1 0.3 16.7 5.0 0.7 3802 0.5 2.5(a) 18.5(b) 3.1 1.1
i-P/
0.2
1.0
2.2(a) 7.5(b) 10.4
2.2(b) 7.5(b)
3,1 9.9 0.3 1.1 18.4 0.8 45.4 0,5
2-Perrtyl
0,l
0.9
2.1(a) 7,6(b) 9,5
2,1(a) 7.6(b)
4.1 602 0.2 3.3 18.1 1.2 43.9 0.5
3.Penryl
0.7
1.5
1,9(a) 4,7 0,04
12.7 3.6 2.2 40.5 0.3
14.8 2.2 0.9 43.2 0.4 OJ 1,9(a) 19,9 0,3
088
0,9
0.3 1S 14.5
28 8,1 1.9
3.8 4.5
Cyclopetrfyl
3.3 4.8
rertPerrtyl
0.4
1.0
1.2 9.3
2.3 4.4 0.4
3.9 6.6 0.3 16.4 3.4 1.0 40.2 0.4
Cyclohyl
0.1
1.0
7.3 39.1
17.6
0.8
1.5 2.5
to,7
11.6 2,3
PII la)
(a), (b), (c) : In a given column, (a) is indistinguishable horn (a), (b) from (I-J),(c) from (c). There are also tin-containing fragment-ions: (d)at m/e 165 (intensity 1.0) (6) at m/e 185 (intensity 2.1): m/e 145 (SnC,H+) (intensity 2) (e) at m/e 165 (intensity J,6) (II) at I@ 165(MeSn”) (2.3); m/e 197 (PhSn*) (0,3); tn/e 226 [Me(PhCHI)Sn”] (0.2) (f) at m/e 189 (intensity 9.4) (i) at m/e 165(2.7); m/e 197(5.8); m/e 213 (PhMeSnH+) (3.1); ra/e 227 (PhMe,Sn+) (23.2); m/c 303 (0.2)
70 eV MASS SPECTRA OF A SERIES OF RMe,-s-BuSn COMPOUNDS
Y!4 TABLE I i
9
c
1.1
0.8
0.8 11,6 0.1
0.3 15.6 4.8
0.4 17.1 1.7 33.0 0.4
5.8 3.3
lkr12yl (N
‘1 *
0.1
2.9
1.2 35.6
0.2 1.6 1.0
92 0.1 0.8 6.7 0,2
2,l 2.8
Neophyl (0
F $
0
6 G “2
g
ORGANOMETALLIC TABLE
XXXVII
SPECTR4
Fragment
OF A SERIES
M&n+ MeSnHf Me,Sn’ Me,SnH ’ B&n+ MeBuSnH+ Me,BuSn+ Bu,MeSn+ Bu,Me$Sn+
OF RMe,-s-BuSn
R=i-Bu
R = n-Bu
Sn+ SnH+ SnH$
4.6 7.0 0.3
LO 14.7 0.2
-
15.6 5.1 2:;
18 4.2 30.8 40.3 1.0 3.6 14.1 0.7 0.3
15.3 2.6 1.8 46.7 0.6 2.9 20.8 1.3 0.3
1.1 3.9 20 1.0 0.1
COMPOUNDS
R=t-Bu 4.8 3.2
3
70 eV MASS
SPECTRA
OF A SERIES
OF RMes[Ph(CHs)CH]Sn
There are also tin-containing fragment-ions: (g) at m/e 213 (intensity 0.9) and m/e 185 (intensity (h) at m/e 277 (intensity 0.2)
FragmenP
R=Et
Sn’ SnH+ MeSn+ MeSnH2f MeaSn+ Me,SnH+ Me&t+ PhSn’ PhenSn+ PhenSnH; MePhenSn’ MePhenSnH+ MesPhenSn+ RSn+ RSnH: RMeSnH’ RMezSn* RPhenSn’ RPhenSnH+ RPhenMeSn+ RPhenMe$n+ a Phen=
283
2
70 eV MASS
TABLE
COMPOUNDS.
i-Bu
(i) at m/e 185 (intensity 3.0) (j) at m/e 260 (intensity 0.2) and m/e 185 (intensity 1.1)
Pr
i-Pr
@)
(h)
4.9 6.6 12.6 0.7
4.0 5.3 12.4 1.7
4.7 6.1 12.9 0.6
3.8 5.8 13.3 0.7
2.5 5.5 12.7 1.0
1.8 3.5 9.9 0.3
3.0 5.3 14.2 0.8
29.7
44
33.6
51.3 1.0 1.4 1.0
44 1.3
26.9 4.6 1.7 2.1 0.2 0.3 0.3 19.4
52 0.5 1.3 0.2
s-Bu
t-Bu
i-Pentyl
Ph
1.9 1.1
0.1 1.7(a) 0.9 6.7 29.4 1.7(a) 1.5 2.2
Chem., 46 (1972)
Neophyl
ii) 7.2 2.3 6.1 3.4
Ph(CH,)CH.
J. Orgonometal.
19)
COMPOUNDS
1.2 1.7 4.6 8.1 30.7
0.1 1.2 1.0 0.8 1.0 21.5
0.2 0.2 4.3 0.9 0.1 1.3 30
0.4
1.5 1.7 0.7 0.3 0.2 2.0 0.3
0.7 18.2
1.3 18.6
0.7 20.9
0.5 18.8
1.5 52.8 02
0.8 37.5
0.9 2.2
1.2 2.2
0.5 1.2
0.8 1.5
2.2 3.7
0.7 0.7
0.8 1.3
1.4
1.0 0.2
1.6
0.4
0.3 1.6 0.4
14.8(a)
11.7
1.3 3.2 5.0 14.8(a)
0.8 1.7
M. GIELEN,
284 TABLE
4
70 eV MASS Fragment Stlf SllH+ SnHf M&n+ MeSnH; EtSn’ EtSnHz PrSn+ PrSnHf BuSnf BuSnH; BuMeSnH+ BuEtSnH+ BuPrSnH+ Bu,SnH + Bu$nMe+ Bu,SnEt+ Bu,SnPr+ Bu,Sn’ Bu$nMe+ Bu$nPr+
SPECT’BA
OF
ALKYLTRIISOBUTYLTINS
R=Me
R=PP
2.3 5.9 0.2 10.4 13.4 0.4 8.8 0.2 1.0
3.3 9.5 2.0 0.3 0.4 0.5 1.3 1.5 6.4
2.4 1.9 32 4.5 4.0 1.4
18.8 1.2 2.3 12.0 21.8
3.8
14.1 0.1
R = i-Pp 3.5 9.7 1.7 5.7 0.7 1.6 9.8 3.7 18.6 0.7 1.4 12.0 17.7
0.4 0.8 4.5 9.2.
0.4 0.07
0.4 0.6 3.7 8.3 0.2
LIThere is also a tin-containing fragment-ion corresponding taining fragment-ion corresponding to BuMeSn+ (0.4). TABLE
G. MAYENCE
tc BuPrSn+
(0.2). b There is also a tin-con-
5
70 eV MASS Fragment
SPECTR4
OF
TRIMETHYLTIN
Me,SnX
x=cz
X=Br
x=1
1.9
OS
41.4 5.2 14.5 :7.8 0.06 2.5 9.8 1.9
40.7 6.6 12.2 18.6
3.5 47.3 9.4 6.0 10.9 0.5 5.1 9.5 1.s 1.7
4.9 19.7 6.0 12.3 31.6 0.2 2.6 14.8 3.6 2.1 7.7
X=F
Me,SnX’C Me S&+ Me&rX+ St%+ Me&r+ Me,SnH _ bfe,SnM&Q CH,Sn’ SnH’ Sn+
HALIDES
0.5 5.9 8.7 2.5 1.5 5.7
1.3 5.7
5.8
Mass spectra at lower potentials (see e.g. fig. 1 to 6) confirm the sequence for the ease of cleavage of a carbon-tin bond of the molecular ion previously described3, viz. Ph(CH3)CH - PhCHz > s-Bu 2 2-Pent Z Cyclopent 2 Cyclohex > i-BukPr-Bu>Me J. Orgunometal. Chem.,
46 (1972)
ORGANOMETALLIC
COMPOUNDS.
285
XXXVII
.
Ma+
6 Me.+nPr* * M+SnH+ 0 Me.-$nBu*
Fig. I.
25
Fig. 2.
Table 3 shows the mono-isotopic spectra of alkyl- and phenyldimethyl(oc-methylbenzyl)tins_ The same type of fragmentation pattern describes the fate of the molecular ion. The mass spectra of alkyltriisobutyltins are presented in Table 4, and show rather unexpected fragments corresponding to cleavage of carbon-carbon bonds (up to 19% of the sum of the intensities of ali fragments for i-Bu,SnMe). All the expected fragments are present. .I. Organometal. Chem, 46 (1972)
286
M. GIELEN, G. MAYENCE
25
r Fig.3.
Z-Pent-s-BuMe.$n
0 M” I Me$inPent* A Me.$nBu* f3 Me$nH*
Fig.4. The 70 eV mass spectra of trimethyltin halides, which have been synthesized for a y-spectroscopy investigation4, are summarized in Table 5. All the expected2 fragments are present. J. Orgmomeral.
Chem., 46 (1972)
ORGANOMETALLIC
COMPOUNDS.
Cyclopent-s-BuMe$n
287
XXXlrII
.
M”
A Me.$IyclopPentSn* l Me,BuSn’ n Me2SnH’
Fig. 5. Cyclohex-s-BuMe$n
. Mm+ A Me$nCyclohex+ 0 Me$nBu* m MqSnH+
20 eV Fig. 6. ACKNOWLEDGEMENTS
The authors are indebted to Mr. C. Moulard for recording the spectra. Financial help from the “Institut pour l’Encouragement de la Recherche Scientifique dans Undustrie et l’Agricxlture”-(I.R.S.I_4.) is gratefully acknowledged (G.M.). REFERENCES 1 M. Gielen, B. De Poorter. M.-T. Sciot and J. Topart, Bull. Sm. Chim. Be/g., in press. 2 M. Gielen, M.-R Barthels, M. De Clercq, C. Dehouck and G. Mayence, J. Organomernl. Chem., 34 (1972) 315. J. Organometal.
Chem, 46 (1972)
288
M. GIELEN,
G. MAYENCE
3 M. Gielen and J. Nasielski, Bull. Sot. Chim. Berg., 77 (1968) 5; S. Bcue. M. GieIen and J. Nasie!ski,
Bull. $oc. Chim. Belg, 77 (1968) 43; M. Gielen and G. Mayence, J. Orgartometal. Chem.. 12 (1968) 363:
S. Boue, M. Gielen. J. Nasielski, J. P. Lieutenant and R. Spielmann, Bull. Sec. Chim. Belg, 78 (1969) 135;
M. Gielen, M.-R. Barthels, M. De Clercq and J. Nasielski, Bull. Sot. Chim. Be/g., 80 (1971) 189; M. Gielen, B. De Poorter. M.-T. Sciot and J. Topart, Bull. Sot. Chim. Belg, in press. 4 J. Devooght, S. Lejeune, M. Gielen, G. Mayence, in preparation; J. Devooght, M. Gielen and S. Lejeune, J. Organometal. Gem, 21 (1970) 333. .I. Organomeral. Chem., 46 (1972)
ORGANOMETALLIC
COMPOUNDS
XXXVII”. MASS SPECTRA METHYLTIN HALIDES
M. GIELEN
281
in The Netherlands
OF MIXED
TETRAALKYLTINS
AND
OF TRI-
and G. MAYENCE
VniversitP Libre de Bruxelles, Faculre des Sciences, Collectifde Roosevelt 50,B1050 Braxelles (Belgium)
Chimie Organique Physique, Avenue F. D.
(Received June 7th. 1972)
SUMMARY
The mass spectra obtained for a series of compounds of alkyldimethyl-secbutyltin, alkyldimetbyl(a-methylbenzyl)tin, alkyltriisobutyltin and trimethyltin halides confirm the fragmentation rules described earlier.
Diastereotopic nonequivalence has been described for molecules of the type R’Me,SnCHY(CH,) with Y =C2H5, C6H5 and with various R’ groups’. The purpose of this paper is to describe the mass spectra of these compounds, and to compare the obtained results with the conclusions of previous studies3. Table 1 gives the observed fragmentions for a series of alkyl- and phenyldimethyl-set-butyltins. Table 2 presents the mass spectra of various dibutyldimethyltins. The results may be summarized in the following possible fragmentation pattern :
SnH’
_
SnH3* _
SnH+
(continued on p. 284) l
For part XXXVI see ref. 1.
J. Organometal. Chem., 46 (1972)
tn $ : 8 w s
R=Er
3.4 5.1 0.4 11.7 3.7 1.2 32.2(a) 2.5 21.3(b)
6.7(c) 1.5
32.2(a) 7.1 21.3(b) 6.7(c)
1.7
0.9
Frofpnenr
Sn+ SnH+ SnH.: MeSn+ MeSnH: Me$n+ Me,SnM + BuSn’ BuSnH: MeBuSnH+ Mc,BuSn’ RSn+
RSnH: MeRSnH’ Me,RSn + BuRSnH’
MeBuRSn +
Me,BuRSn + 0.3
1*1(c)
0.3 2,5(a) 14.0(b)
4.6 7.1 0.2 19.8 4.9 0.4 40.2 0.7 2.5(a) 14.0(b) 2.7 1,2
Pr
0.5
I .2(c)
0.3 2.5(a) 18,5(b)
3.4 7.1 0.3 16.7 5.0 0.7 3802 0.5 2.5(a) 18.5(b) 3.1 1.1
i-P/
0.2
1.0
2.2(a) 7.5(b) 10.4
2.2(b) 7.5(b)
3,1 9.9 0.3 1.1 18.4 0.8 45.4 0,5
2-Perrtyl
0,l
0.9
2.1(a) 7,6(b) 9,5
2,1(a) 7.6(b)
4.1 602 0.2 3.3 18.1 1.2 43.9 0.5
3.Penryl
0.7
1.5
1,9(a) 4,7 0,04
12.7 3.6 2.2 40.5 0.3
14.8 2.2 0.9 43.2 0.4 OJ 1,9(a) 19,9 0,3
088
0,9
0.3 1S 14.5
28 8,1 1.9
3.8 4.5
Cyclopetrfyl
3.3 4.8
rertPerrtyl
0.4
1.0
1.2 9.3
2.3 4.4 0.4
3.9 6.6 0.3 16.4 3.4 1.0 40.2 0.4
Cyclohyl
0.1
1.0
7.3 39.1
17.6
0.8
1.5 2.5
to,7
11.6 2,3
PII la)
(a), (b), (c) : In a given column, (a) is indistinguishable horn (a), (b) from (I-J),(c) from (c). There are also tin-containing fragment-ions: (d)at m/e 165 (intensity 1.0) (6) at m/e 185 (intensity 2.1): m/e 145 (SnC,H+) (intensity 2) (e) at m/e 165 (intensity J,6) (II) at I@ 165(MeSn”) (2.3); m/e 197 (PhSn*) (0,3); tn/e 226 [Me(PhCHI)Sn”] (0.2) (f) at m/e 189 (intensity 9.4) (i) at m/e 165(2.7); m/e 197(5.8); m/e 213 (PhMeSnH+) (3.1); ra/e 227 (PhMe,Sn+) (23.2); m/c 303 (0.2)
70 eV MASS SPECTRA OF A SERIES OF RMe,-s-BuSn COMPOUNDS
Y!4 TABLE I i
9
c
1.1
0.8
0.8 11,6 0.1
0.3 15.6 4.8
0.4 17.1 1.7 33.0 0.4
5.8 3.3
lkr12yl (N
‘1 *
0.1
2.9
1.2 35.6
0.2 1.6 1.0
92 0.1 0.8 6.7 0,2
2,l 2.8
Neophyl (0
F $
0
6 G “2
g
ORGANOMETALLIC TABLE
XXXVII
SPECTR4
Fragment
OF A SERIES
M&n+ MeSnHf Me,Sn’ Me,SnH ’ B&n+ MeBuSnH+ Me,BuSn+ Bu,MeSn+ Bu,Me$Sn+
OF RMe,-s-BuSn
R=i-Bu
R = n-Bu
Sn+ SnH+ SnH$
4.6 7.0 0.3
LO 14.7 0.2
-
15.6 5.1 2:;
18 4.2 30.8 40.3 1.0 3.6 14.1 0.7 0.3
15.3 2.6 1.8 46.7 0.6 2.9 20.8 1.3 0.3
1.1 3.9 20 1.0 0.1
COMPOUNDS
R=t-Bu 4.8 3.2
3
70 eV MASS
SPECTRA
OF A SERIES
OF RMes[Ph(CHs)CH]Sn
There are also tin-containing fragment-ions: (g) at m/e 213 (intensity 0.9) and m/e 185 (intensity (h) at m/e 277 (intensity 0.2)
FragmenP
R=Et
Sn’ SnH+ MeSn+ MeSnH2f MeaSn+ Me,SnH+ Me&t+ PhSn’ PhenSn+ PhenSnH; MePhenSn’ MePhenSnH+ MesPhenSn+ RSn+ RSnH: RMeSnH’ RMezSn* RPhenSn’ RPhenSnH+ RPhenMeSn+ RPhenMe$n+ a Phen=
283
2
70 eV MASS
TABLE
COMPOUNDS.
i-Bu
(i) at m/e 185 (intensity 3.0) (j) at m/e 260 (intensity 0.2) and m/e 185 (intensity 1.1)
Pr
i-Pr
@)
(h)
4.9 6.6 12.6 0.7
4.0 5.3 12.4 1.7
4.7 6.1 12.9 0.6
3.8 5.8 13.3 0.7
2.5 5.5 12.7 1.0
1.8 3.5 9.9 0.3
3.0 5.3 14.2 0.8
29.7
44
33.6
51.3 1.0 1.4 1.0
44 1.3
26.9 4.6 1.7 2.1 0.2 0.3 0.3 19.4
52 0.5 1.3 0.2
s-Bu
t-Bu
i-Pentyl
Ph
1.9 1.1
0.1 1.7(a) 0.9 6.7 29.4 1.7(a) 1.5 2.2
Chem., 46 (1972)
Neophyl
ii) 7.2 2.3 6.1 3.4
Ph(CH,)CH.
J. Orgonometal.
19)
COMPOUNDS
1.2 1.7 4.6 8.1 30.7
0.1 1.2 1.0 0.8 1.0 21.5
0.2 0.2 4.3 0.9 0.1 1.3 30
0.4
1.5 1.7 0.7 0.3 0.2 2.0 0.3
0.7 18.2
1.3 18.6
0.7 20.9
0.5 18.8
1.5 52.8 02
0.8 37.5
0.9 2.2
1.2 2.2
0.5 1.2
0.8 1.5
2.2 3.7
0.7 0.7
0.8 1.3
1.4
1.0 0.2
1.6
0.4
0.3 1.6 0.4
14.8(a)
11.7
1.3 3.2 5.0 14.8(a)
0.8 1.7
M. GIELEN,
284 TABLE
4
70 eV MASS Fragment Stlf SllH+ SnHf M&n+ MeSnH; EtSn’ EtSnHz PrSn+ PrSnHf BuSnf BuSnH; BuMeSnH+ BuEtSnH+ BuPrSnH+ Bu,SnH + Bu$nMe+ Bu,SnEt+ Bu,SnPr+ Bu,Sn’ Bu$nMe+ Bu$nPr+
SPECT’BA
OF
ALKYLTRIISOBUTYLTINS
R=Me
R=PP
2.3 5.9 0.2 10.4 13.4 0.4 8.8 0.2 1.0
3.3 9.5 2.0 0.3 0.4 0.5 1.3 1.5 6.4
2.4 1.9 32 4.5 4.0 1.4
18.8 1.2 2.3 12.0 21.8
3.8
14.1 0.1
R = i-Pp 3.5 9.7 1.7 5.7 0.7 1.6 9.8 3.7 18.6 0.7 1.4 12.0 17.7
0.4 0.8 4.5 9.2.
0.4 0.07
0.4 0.6 3.7 8.3 0.2
LIThere is also a tin-containing fragment-ion corresponding taining fragment-ion corresponding to BuMeSn+ (0.4). TABLE
G. MAYENCE
tc BuPrSn+
(0.2). b There is also a tin-con-
5
70 eV MASS Fragment
SPECTR4
OF
TRIMETHYLTIN
Me,SnX
x=cz
X=Br
x=1
1.9
OS
41.4 5.2 14.5 :7.8 0.06 2.5 9.8 1.9
40.7 6.6 12.2 18.6
3.5 47.3 9.4 6.0 10.9 0.5 5.1 9.5 1.s 1.7
4.9 19.7 6.0 12.3 31.6 0.2 2.6 14.8 3.6 2.1 7.7
X=F
Me,SnX’C Me S&+ Me&rX+ St%+ Me&r+ Me,SnH _ bfe,SnM&Q CH,Sn’ SnH’ Sn+
HALIDES
0.5 5.9 8.7 2.5 1.5 5.7
1.3 5.7
5.8
Mass spectra at lower potentials (see e.g. fig. 1 to 6) confirm the sequence for the ease of cleavage of a carbon-tin bond of the molecular ion previously described3, viz. Ph(CH3)CH - PhCHz > s-Bu 2 2-Pent Z Cyclopent 2 Cyclohex > i-BukPr-Bu>Me J. Orgunometal. Chem.,
46 (1972)
ORGANOMETALLIC
COMPOUNDS.
285
XXXVII
.
Ma+
6 Me.+nPr* * M+SnH+ 0 Me.-$nBu*
Fig. I.
25
Fig. 2.
Table 3 shows the mono-isotopic spectra of alkyl- and phenyldimethyl(oc-methylbenzyl)tins_ The same type of fragmentation pattern describes the fate of the molecular ion. The mass spectra of alkyltriisobutyltins are presented in Table 4, and show rather unexpected fragments corresponding to cleavage of carbon-carbon bonds (up to 19% of the sum of the intensities of ali fragments for i-Bu,SnMe). All the expected fragments are present. .I. Organometal. Chem, 46 (1972)
286
M. GIELEN, G. MAYENCE
25
r Fig.3.
Z-Pent-s-BuMe.$n
0 M” I Me$inPent* A Me.$nBu* f3 Me$nH*
Fig.4. The 70 eV mass spectra of trimethyltin halides, which have been synthesized for a y-spectroscopy investigation4, are summarized in Table 5. All the expected2 fragments are present. J. Orgmomeral.
Chem., 46 (1972)
ORGANOMETALLIC
COMPOUNDS.
Cyclopent-s-BuMe$n
287
XXXlrII
.
M”
A Me.$IyclopPentSn* l Me,BuSn’ n Me2SnH’
Fig. 5. Cyclohex-s-BuMe$n
. Mm+ A Me$nCyclohex+ 0 Me$nBu* m MqSnH+
20 eV Fig. 6. ACKNOWLEDGEMENTS
The authors are indebted to Mr. C. Moulard for recording the spectra. Financial help from the “Institut pour l’Encouragement de la Recherche Scientifique dans Undustrie et l’Agricxlture”-(I.R.S.I_4.) is gratefully acknowledged (G.M.). REFERENCES 1 M. Gielen, B. De Poorter. M.-T. Sciot and J. Topart, Bull. Sm. Chim. Be/g., in press. 2 M. Gielen, M.-R Barthels, M. De Clercq, C. Dehouck and G. Mayence, J. Organomernl. Chem., 34 (1972) 315. J. Organometal.
Chem, 46 (1972)
288
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